3-Pyridinecarboxaldehyde → HCID 22036171, compound

Participants

Reaction Steps

To 2.0 mL (16.07 mmol) of 4-(methylthio)aniline dissolved in 25 mL dichloromethane was added 1.52 mL (16.07 mmol) 3-pyridinecarboxaldehyde, followed by 5.11 g (24.11 mmol) sodium triacetoxyborohydride. The mixture was stirred at room temperature for 4 h, partitioned between EtOAc and brine, dried over MgSO4 and concentrated. Column chromatography, eluting with ethyl acetate/hexane, provided 3.70 g of 4-[(pyridin-2-ylmethyl)amino]thioanisole, pure by 1H NMR.

Provenance & Evidence